JP2001516769A - Use of quaternary carboxylic acid alkanolamine ester salts as antibacterial agents - Google Patents

Abstract

A process for destroying or preventing the proliferation of microorganisms involving contacting the microorganisms with a quaternary carboxylic acid alkanolamine ester salt corresponding to formula I:wherein R1CO is an acyl group having from 2 to 18 carbon atoms, R2 and R3, independently of one another, represent an alkyl group containing from 1 to 16 carbon atoms, or a group corresponding to CH2CH2OR5, R4 is an alkyl group containing from 1 to 4 carbon atoms, R5 is hydrogen and/or R1CO, and X is an anion; is disclosed.

Description

DETAILED DESCRIPTION OF THE INVENTION

TECHNICAL FIELD The present invention relates to antimicrobial agents, especially quaternary carboxylic acids as antimicrobial agents in detergents, disinfectants, preservatives, textile softeners, cosmetics, cooling lubricant emulsions and coating compositions. It relates to the use of alkanolamine ester salts. The present invention also relates to detergents, textile softeners, disinfectants, cosmetics, preservatives, coating compositions and cooling lubricant emulsions containing such quaternary carboxylic acid alkanolamine ester salts.

BACKGROUND OF THE INVENTION Antimicrobial agents are commonly used to inhibit the growth of microorganisms or to kill microorganisms completely. Heretofore, quaternary ammonium compounds, such as benzalkonium chloride or cetyltrimethylammonium chloride, have been used as useful antimicrobial agents. However, such compounds have been found not to be readily biodegradable in sewage treatment plants. Thus, there is a need for antibacterial compounds having performance comparable to such quaternary ammonium compounds and having significantly improved biodegradability.

US Pat. No. 3,910,971 discloses a quaternary carboxylic acid alkanolamine ester salt obtained by reacting 2-dimethylamino-2-methyl-1-propanol with a fatty acid, followed by quaternization, as an antibacterial agent. Has been described. However, such compounds have little effect on the gram-negative bacterium Pseudomonas aeruginosa, which is disadvantageous, inter alia, because product contamination is caused by this commonly found waterborne bacterium.

[0004] European patent application EP 0 461 419 describes poly (oxyalkylene) aminoalkanol esters and their ammonium compounds, which are also stated to exhibit antibacterial activity. However, the compounds have at least one hydroxyisopropyl group and a methyl group on the nitrogen atom. The effect of such compounds on fungi, especially on the normally present Pseudomonas aeruginosa, is not described.

(Disclosure of the Invention) (Technical Problems to be Solved by the Invention) An object of the present invention was to provide an antibacterial compound having an antibacterial activity comparable to that of a conventional quaternary ammonium compound. Such compounds also exhibit, inter alia, antimicrobial activity against the normally existing fungus Pseudomonas aeruginosa.
Moreover, such compounds exhibit better biodegradability than conventional quaternary ammonium compounds.

(Solution) It has been found that certain quaternary carboxylic acid alkanolamine ester salts satisfy such conditions. That is, the present invention provides a compound of the formula (I):

Embedded image[Where R¹CO is an acyl group having 2 to 18 carbon atoms;^TwoAnd R^ThreeIs an alkyl group having 1 to 16 carbon atoms or a group CH _Two -CH_Two-OR^FiveAnd R^FourIs an alkyl group having 1 to 4 carbon atoms;^FiveIs hydrogen and / or R¹CO and X^-Is an anion. The quaternary carboxylic acid alkanolamine ester salt represented by the formula:
About use.

[0007] Such quaternary carboxylic acid alkanolamine ester salts are compounds known from the literature and are often referred to as "esterquats". Such compounds are typically synthesized by esterifying an alkanolamine with a carboxylic acid in the presence of hypophosphorous acid, passing air through the reaction mixture, and then quaternizing the esterified product. Examples of extensive prior art documents in this regard are US 3,158,867, US 4,370,272, EP-A-0239910, EP
-A-0293955, EP-A-0295739 and EP-A-03090
52 is quoted here.

According to the present invention, a quaternary carboxylic acid alkanolamine ester salt is synthesized by known methods of formula (II):

Embedded image R ² —N—CH ₂ CH ₂ OH (II) | R ^{3 wherein} R ² and R ³ have the same meaning as in formula (I), but R ² and / or R ³ Is a group CH ₂ CH ₂ OR ⁵ , then R ⁵ is hydrogen. Is esterified with a carboxylic acid of the formula R ¹ COOH. Alkanolamines (II) may be transesterified with esters of the above carboxylic acids to produce compounds (I) for use in accordance with the present invention.

Suitable alkanolamines are dialkylethanolamines (R ² , R ³ = alkyl groups having 1 to 16 carbon atoms), such as dimethylethanolamine, methylethylethanolamine, diethylethanolamine, methylbutylethanolamine and / or methylhexyl ethanolamine, monoalkyl diethanolamine _{^{(R 2 = CH 2 CH 2}} OH; R 3 = C 1-16 alkyl group), such as methyl diethanolamine, ethyl diethanolamine and / or butyl diethanolamine, and / or triethanolamine (R ² , R ³ = CH ₂ CH ₂ OH).
Preference is given to using monoalkyldiethanolamine and / or triethanolamine.

Suitable carboxylic acids R ¹ COOH are aliphatic saturated and / or unsaturated carboxylic acids, especially aliphatic saturated carboxylic acids, such as acetic acid, propionic acid, butyric acid, caproic acid, caprylic acid, capric acid, pelargonic acid, Lauric acid, myristic acid, palmitic acid and industrial mixtures thereof (obtained, for example, by pressure hydrolysis of natural fats and oils). An aliphatic saturated carboxylic acid having 8 to 12 carbon atoms is preferable, that is, R ¹ CO in the formula (I) is preferably an aliphatic saturated acryl group having 8 to 12 carbon atoms.

The ratio of the carboxylic acid or carboxylic acid ester to the alkanolamine depends on the desired degree of esterification of the free hydroxyl groups of the alkanolamine. In the case of the preferred monoalkyldiethanolamine and triethanolamine,
All or only some of the free hydroxyl groups can be esterified with a carboxylic acid. When esterified, R ⁵ in formula (I) is R ¹ CO. Esterification can be complete or partial. In the case of partial esterification, the average degree of esterification of (total) free hydroxyl groups is preferably from 1.2 to 1.2 for monoalkyldiethanolamine.
1.7, and preferably 1.2 to 2.5 for triethanolamine. That is, there is a mixture of di- or triethanolamine carboxylic acid mono-, di- and optionally triesters. According to the invention, at least two of the free hydroxyl groups of triethanolamine are esterified with a carboxylic acid. Instead of the carboxylic acid, its ester derivative may be reacted with an alkanolamine.

Subsequent quaternization is performed by methods known in the art to produce the quaternary carboxylic acid alkanolamine ester salt (I). Formula R ⁴ X wherein R ⁴ has the same meaning as in Formula (I) and is preferably a methyl group. Are used for quaternization. When X in formula (I) is formate, acetate, tartrate, dicarboxylate, citrate, halide, sulfate or nitrate, anion exchange was performed after normal quaternization.

According to the invention, compounds (I) in which R ² is a group CH ₂ CH ₂ OR ⁵ and R ³ is a methyl group, and / or R ² and R ³ are groups CH ₂ CH ₂ OR ⁵ It is particularly preferred to use the compound (I) which is (R ⁵ is as defined above). Examples of particularly suitable compounds include dimethyldiethanolammonium dicaprylate methosulfate, methyltriethanolammonium tricaprylate methosulfate, methyltriethanolammonium dicaprylate methosulfate, and dimethyldiethanolammonium diperargonate methosulfate. Tosulfate.

According to the invention, the compounds described are used as antimicrobial agents. In the context of the present invention, antimicrobial agents are understood to be compounds which can kill or inhibit the growth of bacteria, yeasts, fungi, viruses and protists. The antimicrobial agent thus defined may be used in any product requiring a corresponding effect. The antimicrobial agent is preferably a detergent / cleaner, such as a dishwashing detergent, a multipurpose cleaner, a sanitary cleaner, a textile softener for antibacterial finishing of textiles, a disinfectant, such as a disinfectant for home and hospital use, a preservative. ,
For example, it is used in preservatives for preserving industrial raw materials and products, cooling lubricant emulsions, cosmetics, and coating compositions, such as pastes, paints and timber preservatives.

The compounds used according to the invention are effective in antimicrobial activity in amounts of only> 5 mg / 1 (in terms of active substance, based on the formulation). The compound is typically 5-5000 mg / 1,
It is preferably used in an amount of 50 to 1000 mg / 1 (in terms of active substance, based on the preparation). In the case of concentrates, quaternary carboxylic acid alkanolamine ester salts may be used in larger amounts. However, the use concentration when the end user dilutes the concentrate with water is within the above range.

The compounds used according to the invention can be used in pure form or as a solution. Suitable solvents are water and / or lower alcohols, especially ethanol, propanediol and / or isopropanol. 6 carbon atoms
Especially for quaternary carboxylic acid alkanolamine ester salts of the type having more than two acyl groups, it is preferred to use lower alcohols or aqueous mixtures thereof.

The present invention relates to a detergent / cleaner containing a quaternary carboxylic acid alkanolamine ester salt as an antibacterial agent, a preservative containing a quaternary carboxylic acid alkanolamine ester salt as an antibacterial agent, a quaternary carboxylic acid alkanol Cosmetics containing amine ester salts as antibacterial agents, disinfectants containing quaternary carboxylic acid alkanolamine ester salts, cooling lubricant emulsions containing quaternary carboxylic acid alkanolamine ester salts, and quaternary carboxylic acid alkanols The present invention also relates to a fabric softener containing an amine ester salt as an antibacterial agent. The quaternary carboxylic acid alkanolamine ester salt may be present in such formulations at the concentrations described above. Furthermore,
Such formulations may, of course, contain other antibacterial agents and other usual ingredients in commonly used amounts.

In the detergent / cleaner, for example, the following anionic, nonionic and / or amphoteric or zwitterionic surfactants can be present: Anionic surfactants: alkylbenzenesulfonates, alkanesulfonates, olefinsulfonates , Alkyl ether sulfonate, glycerol ether sulfonate, methyl ester sulfonate, sulfo fatty acid, alkyl sulfate, fatty alcohol ether sulfate, glycerol ether sulfate, hydroxy mixed ether sulfate, monoglyceride (ether)
Sulfate, fatty acid amide (ether) sulfate, sulfosuccinate,
Sulfosuccinamate, sulfoglyceride, ether carboxylic acid, alkyl oligoglucoside sulfate, alkyl (ether) phosphate, and protein fatty acid condensate.

Nonionic surfactants: fatty alcohol polyglycol ether, alkylphenol polyglycol ether, fatty amine polyglycol ether, fatty acid amide polyglycol ether, fatty acid polyglycol ester, alkoxylated triglyceride, alkyl oligoglycoside, sugar ester, sorbitan ester , Polysorbates, polyol fatty acid esters, amine oxides, fatty acid alkanolamides, alkyl lactams, and fatty acid-N-alkyl glucamides. Amphoteric or zwitterionic surfactants: alkylamidobetaines, aminopropionates, aminoglycinates, imidazolinium betaines, and sulfobetaines.

The detergent / cleaner may also contain the usual ingredients such as builders, salts, bleaches, optical brighteners, anti-redeposition agents, solubilizers and enzymes. Preservatives may contain alcohols, aldehydes, acids, esters, phenols, terpenes and / or complexing agents. Disinfectants may also contain one or more of the anionic, nonionic and / or amphoteric or zwitterionic surfactants, as well as water, alcohol, complexing agents and other antimicrobial compounds.

Cooling lubricant emulsions typically consist of an aqueous phase and an organic phase, the organic phase typically comprising
Formed from mineral or vegetable oils. In addition, they often contain emulsifiers, optionally high-pressure additives, corrosion inhibitors and / or complexing agents. Cosmetics also include one or more of the above-described anionic, nonionic and / or amphoteric or zwitterionic surfactants, optionally water or aqueous phases, alcohols, optionally oil phases, emulsifiers, and optionally other Of an antimicrobial compound. Conventional additives such as abrasives, pearlescent pigments, dyes, fragrances, and optionally other preservatives, gel formers, and / or conditioning and care ingredients may be present.

Embodiment A. Antimicrobial activity The following selected test bacteria were tested for the antimicrobial activity of the quaternary carboxylic acid alkanolamine ester salts used according to the invention against the following test bacteria: a) Staphylococcus aureus ATCC 6538 b) Pseudomonas aeruginosa ATCC 15442 c) Candida albicans ATCC 10231

The efficacy of the test compound was determined using Deutsche Gesellschaft fuer Hygiene und Mikrobiol
ogie (DGHM) was evaluated by a suspension test according to the guidelines. Test solutions containing the quaternary carboxylic acid alkanolamine ester salts in the amounts shown in the table at 50, 100, 200, 400 and 800 mg / l were prepared using water with a hardness of 17 ° dH and optionally isopropanol.

At room temperature, 0.1 ml of the test bacterial suspension was placed in a test tube containing 10 ml of the test solution.
ml was pipetted and mixed. After a contact time of 5, 15, 30 and 60 minutes, a 1 ml sample is pipetted from the test tube and an inactivator solution (inactivator:
3.0% Tween, 0.3% lecithin, 0.1% histidine). After inactivation for at least 5 minutes, at most 30 minutes, casein-peptone-soy flour peptone (CaSo) -agar plates were inoculated for viable cell counts. The inactivation mixture was inoculated directly onto CaSo-agar using a spiral plater. The samples were incubated at 37 ° C for 24-72 hours and evaluated for growth visually. In this way, the death time or the number of remaining bacteria was measured. The number of bacteria in the water control to which no bacteria were added and the number of bacteria in the inactivated test solution were compared in consideration of dilution. The log reduction factor (i.e., reduction expressed by a power of 10) is shown in the table below. The higher the value, the higher the antibacterial properties. The symbol "<" indicates that the log reduction factor is less than the stated value, and ">" indicates that it is greater than the stated value. The abbreviation CU means “use concentration”.

The following compounds were tested: Example 1: dimethyldiethanolammonium dicaprylate methosulfate Example 2: methyltriethanolammonium tricaprylate methosulfate Example 3: dimethyldiethanolammonium dipelargonic acid ester Tosulfate Example 4: Trimethylethanol ammonium coconut oil fatty acid ester methosulfate Example 5: Methyl triethanol ammonium dilaurate methosulfate Example 6: Methyl triethanol ammonium dicaprate methosulfate Example 7: Methyl triethanol ammonium dicaprylate methosulfate Example 8: Dimethyl diethanol ammonium dilaurate methosulfate Example 9: Example 10: dimethyldiethanolammonium dicaprate methosulfate Methyltriethanolammonium tricaprate methosulfate

Example 1: Dimethyl diethanol ammonium dicaprylate methosulfate

[Table 1] Staphylococcus aureus ATCC 6538 Number of bacteria 2.73 · 10 ⁷ / ml CU [mg / l] 50 100 200 400 800 After 5 minutes <1.32 <1.32 <1.32 <1.32 <1.32 After 15 minutes <1.71 <1.71 <1.71 < 1.1 <3.59 After 30 minutes <1.23 <1.23 <1.23 1.95 <3.96 After 60 minutes <1.32 <1.32 <1.32 3.54> 5.32

[0027]

[Table 2] Pseudomonas aeruginosa ATCC 15442 Number of bacteria 4.23 · 10 ⁷ / ml CU [mg / l] 50 100 200 400 800 After 5 minutes <1.83 <1.83 <1.83 <1.83> 5.83 After 15 minutes <1.47 <1.47 <1.47 <1.47> 5.47 After 30 minutes <1.55 <1.55 <1.55 3.22> 5.55 After 60 minutes <1.56 <1.56 <1.56 4.41> 5.56

[0028]

[Table 3] Candida albicans ATCC 10231 bacterial count 2.59 · 10 ⁶ / ml CU [mg / l] 50 100 200 400 800 After 5 minutes <0.50 <0.50 1.53>4.5> 4.50 After 15 minutes <0.37 0.41 2.53>4.37> 4.37 After 30 minutes <0.35 0.60 2.91>4.35> 4.35 After 60 minutes <0.36 0.70 3.61>4.36> 4.36

Example 2: Methyl triethanol ammonium tricaprylate methosulfate

[Table 4] Staphylococcus aureus ATCC 6538 Number of bacteria 1.44 ・ 10 ⁷ / ml CU [mg / l] 50 100 200 400 800 After 5 minutes 3.21 3.54 4.32>5.56> 5.56 After 15 minutes>5.38>5.38>5.38>5.38> 5.38 After 30 minutes>5.50>5.50>5.50>5.50> 5.50 After 60 minutes>5.41>5.41>5.41>5.41> 5.41

[0030]

[Table 5] Pseudomonas aeruginosa ATCC 15442 Number of bacteria 6.27 ・ 10 ⁷ / ml CU [mg / l] 50 100 200 400 800 After 5 minutes <1.38 <1.38 1.38 4.08 4.42 After 15 minutes <1.70 3.25 3.95>5.70> 5.70 30 minutes After 3.31 3.75 4.40>5.68> 5.68 After 60 minutes 3.98 4.49>5.59>5.59> 5.59

[0031]

[Table 6] Candida albicans ATCC 10231 Number of bacteria 6.91 ・ 10 ⁶ / ml CU [mg / l] 50 100 200 400 800 After 5 minutes 3.44>4.73>4.73>4.73> 4.73 After 15 minutes>4.71>4.71>4.71> 4.71 > 4.71 after 30 minutes>4.82>4.82>4.82> 4.82 <4.82 after 60 minutes>4.68>4.68>4.68>4.68> 4.68

Example 3 Dimethyl Diethanol Ammonium Diperargonate Methosulfate

[Table 7] Staphylococcus aureus ATCC 6538 bacterial count 2.41 ・ 10 ⁷ / ml CU [mg / l] 50 100 200 400 800 5 minutes later <1.31 <1.31 2.05 3.25 3.78 15 minutes later 2.31 3.67>5.74>5.74> 5.74 30 minutes After 3.01>5.19>5.19>5.19> 5.19 After 60 minutes 4.85>5.55>5.55>5.55> 5.55

[0033]

[Table 8] Pseudomonas aeruginosa ATCC 15442 Number of bacteria 5.09 ・ 10 ⁷ / ml CU [mg / l] 50 100 200 400 800 After 5 minutes <1.59 4.36>5.59>5.59> 5.59 After 15 minutes 2.99>5.58>5.58>5.58> 5.58 After 30 minutes 3.58>5.67>5.67>5.67> 5.67 After 60 minutes 3.77>5.53>5.53>5.53> 5.53

[0034]

TABLE 9 Candida albicans ATCC 10231 bacteria number ^{4.82 · 10 6 / ml CU [} mg / l] 50 100 200 400 800 5 min after 2.86>4.63>4.63>4.63> 4.63 after 15 minutes>4.63>4.63>4.63> 4.63 > 4.63 after 30 minutes>4.66>4.66>4.66>4.66> 4.66 after 60 minutes>4.67>4.67>4.67>4.67> 4.67

Example 4: Trimethylethanolammonium coconut oil fatty acid ester methosulfate 75% in isopropanol

[Table 10] Staphylococcus aureus ATCC 6538 Number of bacteria 2.05 ・ 10 ⁷ / ml CU [mg / l] 50 100 200 400 800 After 5 minutes <1.51 <1.51 <1.51 2.33 3.12 After 15 minutes <1.36 1.78 3.4 4.14> 5.36 30 minutes After <1.38 3.03 4.38>5.38> 5.38 After 60 minutes 1.94 4.02>5.26>5.26> 5.26

[0036]

[Table 11] Pseudomonas aeruginosa ATCC 15442 Number of bacteria 5.77 ・ 10 ⁷ / ml CU [mg / l] 50 100 200 400 800 After 5 minutes <1.51 <1.51 <1.51 <1.51 4.02 After 15 minutes <1.66 <1.66 <1.66 3.9> 5.66 After 30 minutes <1.46 <1.46 <1.46>5.66> 5.66 After 60 minutes <1.47 <1.47 <3.35>5.47> 5.47

[0037]

[Table 12] Candida albicans ATCC 10231 Number of bacteria 7.05 ・ 10 ⁷ / ml CU [mg / l] 50 100 200 400 800 After 5 minutes <0.80 1.19 3.43>4.80> 4.80 After 15 minutes <0.79 3.01>4.79>4.79> 4.79 After 30 minutes 0.91>4.80>4.80>4.80> 4.80 After 60 minutes 1.40>5.05>5.05>5.05> 5.05

Example 5: Methyl triethanol ammonium dilaurate methosulfate

[Table 13] Staphylococcus aureus ATCC 6538 Number of bacteria 5.95 / 10 ⁹ / ml CU [mg / l] 50 100 200 400 800 After 5 minutes <1.79 <1.79 2.52 2.70 3.85 After 15 minutes <1.73 2.38 4.25>5.73> 5.73 30 minutes After 2.53 3.80>5.75>5.75> 5.75 After 60 minutes 3.88 5.21>5.86>5.86> 5.86

[0039]

[Table 14] Pseudomonas aeruginosa ATCC 15442 Number of bacteria 7.86 / 10 ⁹ / ml CU [mg / l] 50 100 200 400 800 After 5 minutes <1.85 <1.85 <1.85 <1.85 <1.85 After 15 minutes <1.79 <1.79 <1.79 < 1.79 3.43 After 30 minutes <1.71 <1.71 <1.71 <1.71 3.95 After 60 minutes <1.81 <1.81 <1.81 3.84 4.40

Example 6: Methyl triethanolammonium dicaprate methosulfate

[Table 15] Staphylococcus aureus ATCC 6538 Number of bacteria 5.95 / 10 ⁹ / ml CU [mg / l] 50 100 200 400 800 After 5 minutes 4.12 4.58 4.55 4.48 5.44 After 15 minutes>5.73>5.73>5.73>5.73> 5.73 30 minutes After>5.75>5.75>5.75>5.75> 5.75 after 60 minutes>5.86>5.86>5.86>5.86> 5.86

[0041]

[Table 16] Pseudomonas aeruginosa ATCC 15442 Number of bacteria 7.86 / 10 ⁹ / ml CU [mg / l] 50 100 200 400 800 After 5 minutes <1.85 <1.85 <1.85 <1.85 <1.85 After 15 minutes <1.79 <1.79 <1.79 < 1.79 4.14 After 30 minutes <1.71 <1.71 3.35 4.18 4.76 After 60 minutes <1.81 3.19 3.89>5.81> 5.81

[0042]

[Table 17] Candida albicans ATCC 10231 Number of bacteria 8.95 ・ 10 ⁸ / ml CU [mg / l] 50 100 200 400 800 After 5 minutes <0.87 1.27 1.24 1.38 1.33 After 15 minutes 1.64 3.03 3.66 3.51> 4.87 After 30 minutes 1.93 3.75 >4.78>4.78> 4.78 After 60 minutes 2.62 4.15>4.67>4.67> 4.67

Example 7: Methyl triethanol ammonium dicaprylate methosulfate

[Table 18] Staphylococcus aureus ATCC 6538 bacterial count 3.5 · 10 ⁹ / ml CU [mg / l] 50 100 200 400 800 After 5 minutes>5.75>5.75>5.75>5.75> 5.75 After 15 minutes>5.53>5.53>5.53>5.53> 5.53 After 30 minutes>5.42>5.42>5.42>5.42> 5.42 After 60 minutes>5.69>5.69>5.69>5.69> 5.69

[0044]

[Table 19] Pseudomonas aeruginosa ATCC 15442 Number of bacteria 9.14 ・ 10 ⁹ / ml CU [mg / l] 50 100 200 400 800 5 minutes later <1.77 3.64 4.59 5.32> 5.77 15 minutes later <1.72>5.72>5.72>5.72> 5.72 After 30 minutes <1.76> 5.76 5.76>5.76> 5.76 After 60 minutes 3.65>5.86>5.86>5.86> 5.86

[0045]

[Table 20] Candida albicans ATCC 10231 bacteria count 1.81 · 10 ⁸ / ml CU [mg / l] 50 100 200 400 800 After 5 minutes>4.31>4.31>4.31>4.31> 4.31 After 15 minutes>4.18>4.18>4.18>4.18> 4.18 after 30 minutes>4.16>4.16>4.16>4.16> 4.16 After 60 minutes>4.27>4.27>4.27>4.27> 4.27

Example 8: Dimethyl diethanol ammonium dilaurate methosulfate

[Table 21] Staphylococcus aureus ATCC 6538 Number of bacteria 4.23 · 10 ⁹ / ml CU [mg / l] 100 200 400 After 5 minutes <1.39 1.98 2.34 After 15 minutes 3.24 3.40 4.64 After 30 minutes 4.28 5.29> 5.51 After 60 minutes 4.23>5.60> 5.60

[0047]

[Table 22] Pseudomonas aeruginosa ATCC 15442 Number of bacteria 8.5 ・ 10 ⁹ / ml CU [mg / l] 100 200 400 After 5 minutes <1.88 <1.88 <1.88 After 15 minutes <1.93 <1.93 <1.93 After 30 minutes <1.80 <1.80 3.05 after 60 minutes <1.90 3.05 3.77

Example 9: Methyl triethanol ammonium tricaprate methosulfate

[Table 23] Staphylococcus aureus ATCC 6538 Number of bacteria 4.23 · 10 ⁹ / ml CU [mg / l] 50 100 200 After 5 minutes <1.39 <1.39 <1.39 After 15 minutes <1.59 <1.59 <1.59 After 30 minutes <1.51 <1.51 1.83 After 60 minutes <1.60 2.09 2.97

[0049]

[Table 24] Pseudomonas aeruginosa ATCC 15442 Number of bacteria 8.5 ・ 10 ⁹ / ml CU [mg / l] 100 200 400 After 5 minutes <1.88 <1.88 <1.88 After 15 minutes <1.93 <1.93 <1.93 After 30 minutes <1.80 <1.80 3.27 after 60 minutes <1.90 2.94 3.72

Example 10: Dimethyl diethanol ammonium dicaprate methosulfate

[Table 25] Staphylococcus aureus ATCC 6538 Number of bacteria 5.95 / 10 ⁹ / ml CU [mg / l] 100 200 400 After 5 minutes>5.56>5.56> 5.56 After 15 minutes>5.55>5.55> 5.55 After 30 minutes>5.72> 5.72 > 5.72 after 60 minutes>5.69>5.69> 5.69

[0051]

[Table 26] Pseudomonas aeruginosa ATCC 15442 Number of bacteria 9.45 ・ 10 ⁹ / ml CU [mg / l] 100 200 400 5 minutes 3.11 3.54 4.31 15 minutes 3.48 4.51 5.04 30 minutes 3.95 5.50 5.64 60 minutes 4.84 5.44> 5.79

[0052]

[Table 27] Candida albicans ATCC 10231 Number of bacteria 1.03 · 10 ⁹ / ml CU [mg / l] 50 100 After 5 minutes 2.87 4.27 After 15 minutes>4.84> 4.84 After 30 minutes>4.89> 4.89 After 60 minutes>4.80> 4.80

B. Antibacterial activity against other bacteria and fungi Bacteria:-Salmonella enteritidis-Escherichia coli-Enterococcus faecium and fungi:-Microsporum gypseum-Trichophyton mentagrophytes tested methyltriethanolammonium dioctanoate methosulfate as in A) did. The log reduction rate of Example 11 is shown in the following table.

Results of Example 11 Fungi

[Table 28]

[0055]

[Table 29]

Bacteria

[Table 30]

[0057]

[Table 31]

[0058]

[Table 32]

The effect on bacteria was confirmed by the obtained test results. The composition was found to be particularly effective against Gram-positive bacteria. The fungus Microsporum gypseum is almost completely killed at a concentration of 50 mg / l even after the shortest contact time. For dermatophytes Trichophyton mentagrophytes, even without least after a long contact time (60 min), killing activity of about 10 ² starts to be observed.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification FI FI Theme Court ゛ (Reference) // C11D 1/62 C11D 1/62 (72) Inventor Guenter Uhues Germany Day 40789 Monheim, Robert −Koch-Strasse No.45 F term (reference) 4C083 AC691 AC692 CC01 EE01 EE10 EE12 4C206 AA01 AA02 FA42 MA01 MA04 NA14 NA20 ZB35 4H003 AE06 EA24 EB19 4H011 AA02 AA03 BA01 BB04 BB14 BB07 BB14

Claims (13)

[Claims] 1. A compound of formula (I):[Where R¹CO is an acyl group having 2 to 18 carbon atoms;^TwoAnd R^ThreeIs an alkyl group having 1 to 16 carbon atoms or a group CH _Two -CH_Two-OR^FiveAnd R^FourIs an alkyl group having 1 to 4 carbon atoms;^FiveIs hydrogen and / or R¹CO and X^-Is an anion. The quaternary carboxylic acid alkanolamine ester salt represented by the formula:
use. 2. The use according to claim 1, wherein the quaternary carboxylic acid alkanolamine ester salt (I) wherein R ¹ CO is an aliphatic saturated acyl group having 8 to 12 carbon atoms. 3. A quaternary carboxylic acid alkanolamine ester salt (I) wherein R ² is a group CH ₂ CH ₂ OR ⁵ and R ³ is a methyl group.
Use of the description. 4. The use according to claim 1, wherein the quaternary carboxylic acid alkanolamine ester salt (I) is used, wherein R ² and R ³ are groups CH ₂ CH ₂ OR ⁵ . 5. The use according to claim 1, wherein the quaternary carboxylic acid alkanolamine ester salt (I) wherein R ⁴ is a methyl group is used. 6. X is methosulfate, ethosulfate, formate,
The use according to any of claims 1 to 5, which is an anion selected from the group consisting of acetate, tartrate, dicarboxylate, citrate, halide, sulfate, phosphate and nitrate. 7. A quaternary carboxylic acid alkanolamine ester salt (I)
7. Use according to any of the preceding claims for use as an antibacterial agent in detergents, disinfectants, preservatives, cosmetics, textile softeners, cooling lubricant emulsions and coating compositions. 8. A quaternary carboxylic acid alkanolamine ester salt (I)
The formulation is used in an amount of 5 to 5000 mg / 1 in terms of active substance, based on the formulation.
Use according to any one of the preceding items 7. 9. A detergent containing the quaternary carboxylic acid alkanolamine ester salt (I) as an antibacterial agent. 10. A preservative containing a quaternary carboxylic acid alkanolamine ester salt (I) as an antibacterial agent. 11. A disinfectant containing a quaternary carboxylic acid alkanolamine ester salt (I) as an antibacterial agent. 12. A cooling lubricant emulsion containing a quaternary carboxylic acid alkanolamine ester salt (I) as an antibacterial agent. 13. A cosmetic containing the quaternary carboxylic acid alkanolamine ester salt (I) as an antibacterial agent.